Hydrazine → HCID 58504795, compound

Participants

Reaction Conditions

Reaction Steps

Into a microwave tube, (3S)-1-[2-amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-N-(phenylmethyl)-3-piperidinecarboxamide (190 mg, 0.440 mmol), 3 mL of EtOH, Hunig's base (0.31 mL, 1.76 mmol), and hydrazine anhydrous (0.083 mL, 2.64 mmol) were added, and the yellow mixture was heated at 150° C. for 180 minutes under microwave conditions. The solution turned black. LCMS showed mainly product. The black solids were filtered and the yellow filtrate was evaporated. The yellow residue was sonicated in EtOAc at 50° C., and the solid was filtered. This material was then sonicated in water at 50° C., and the solid was filtered and washed with water to afford the title compound (92 mg) as a light yellow solid. LC-MS (ES) m/z=444 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 1.37-1.55 (m, 1H), 1.62-1.80 (m, 2H), 1.96 (m, 1H), 2.35-2.45 (m, 1H), 2.81-3.05 (m, 2H), 4.18-4.46 (m, 3H), 4.56 (m, 1H), 5.38 (s, 2H), 6.10 (s, 2H), 6.65 (s, 1H), 7.25 (d, J=5.8 Hz, 2H), 7.59 (dd, J=8.6, 1.3 Hz, 1H), 7.67-7.78 (m, 1H), 7.96 (s, 1H), 8.45-8.65 (m, 3H), 11.51 (s, 1H).

Provenance & Evidence